Rhythm and blues has a longstanding tradition of flamboyant performers. When most singers were wearing black tuxedos to go with their processed hairdos, a few others took things a step further, adding gold lame, glitter, and wild colors in order to be better seen. Iconic performers like James Brown, Guitar Slim, and Little Richard were among the artists bound and determined to set themselves apart from the pack. However, there was a small subset of R&B performers who took it even further around the bend than that...by dressing as the opposite sex.

Back in the days when you didn't just go to see bands at clubs but rather at full-on revues, drag queens were an accepted part of the entertainment world, particularly in African-American communities. Herman Roberts, who operated the famed Roberts' Show Lounge in Chicago, recalls that the Jewel Box Revue, a noted crossdressing act, played well at his club in the fifties and sixties, even attracting white audiences.

As rhythm & blues and rock & roll started to take a foothold in the 1950s, this overlooked area of entertainment subtly made its way to this new world. Drag-rooted artists like Billy Wright and the aforementioned Little Richard got their start that way, but three other legendary R&B singers made it their life's work.

Bobby Marchan

Originally from Youngstown, Ohio, Bobby Marchan roared out of New Orleans in 1960 with his hit "There Is Something On Your Mind - Part Two." Part One was a version of the Big Jay McNeely tune sung straight. Marchan's absurd monologue was what sold “Part Two,” as he advised how a cheating lover can be stopped with a bullet.

Prior to this, Marchan had been one of the singers with Huey Smith & the Clowns - you can hear his high-pitched, almost feminine voice on their Ace Records single "Don't You Just Know It." Supposedly when Huey Smith and band first met Ace head Johnny Vincent, Marchan was in full, convincing drag and even fooled the label boss.

A teenaged Marchan had founded his own drag revue, the Powder Box Revue. After touring across the country, he noticed that New Orleans was a hotbed for drag entertainment and settled there. Working the Club Tijuana (sometimes under the name "Loberta"), he recorded a few early singles before joining Huey Smith's band between 1956-60. His 1960 solo smash “There Is Something on Your Mind” became and remained his calling card - a follow-up single for the Fire label, "You're Still My Baby - Part Two" repeated a similar monologue formula.

He moved to the Memphis-based Stax subsidiary Volt (apparently on the recommendation of Otis Redding) for "You Won't Do Right," which included a spoken bridge that partially quoted his big hit ("you know it's so hard to be in love with someone..."). The bit would reappeared 20-plus years later with "There Is Something On Your Mind '87," on the Edge label.

Apart from one other release that made the R&B Top 20 in 1966 ("Shake Your Tambourine" on the Cameo imprint), no more hits were forthcoming for Marchan, although he continued to release new singles through the ‘80s, and even helped in founding the hip-hop label Cash Money (which gave us drag superstar Katie Red).

Although his chartmaking days were done, Marchan would occasionally take his wig, tight dress and lipstick out of mothballs to work drag shows here and there until his death in 1999.

Marchan’s 1968 single "Ain't No Reason For Girls To Be Lonely" (on the Gamble label) included advice to ladies on applying the right cosmetics. "Beauty don't come from nowhere but out of a jar," he sang. He certainly knew what he was talking about.

Jackie Shane

The song "Any Other Way" was originally written and recorded by Memphis soul singer William Bell in 1962. The chorus ran: "Tell her that I'm happy/Tell her that I'm gay/Tell her I wouldn't have it/Any other way."

Somehow this lyric meant something different coming from a transgender woman who moved from Nashville to Toronto. Jackie Shane cut the tune for the Sue label at a time when most people thought being "gay" merely meant being happy. (When New York soul singer Chuck Jackson recorded his version, he changed the line to "tell her that I'm free," which doesn't even rhyme.)

When this track was comped on a Sue Records box set in the nineties, the liner notes didn't mention Shane's sexuality. The photos of Shane (who died in February at age 78) show a person wearing the hottest female fashions of that era. For a person with such a commanding voice, Shane surprisingly felt more comfortable on stage than in the studio.

Shane eventually moved to Montreal where, still identifying as a man, she sat in with Frank Motley & the Motley Crew, an R&B revue left over from the jump-blues days. Shane soon became a full member of the band, rocking short skirts and singing with the group until she retired at the beginning of the seventies, moving to Los Angeles to care for her mother before relocating back to Nashville in 1996.

Interest in her discography was re-ignited when the Numero Group released a compilation of her work (Any Other Way) in 2017. This release was nominated for a Grammy, in the Best Historical Album category.

Wilbur “Hi-Fi” White

It's the summer of 1985. The second annual Chicago Blues Festival is underway, downtown in Grant Park. Wilbur "Hi-Fi" White, a legendary singer/comedian, has been chosen to emcee the show. White was a fixture at several blues revues similarly serving as compere, but this time it would be different.

Instead of the all-black crowds he usually worked for, he was standing before a solidly interracial audience in front of the Petrillo Bandshell. Normally he appeared to crowds well over 21; this time around, there were some children in the mix. The show was being simulcast over the radio; usually White's banter didn't go past the walls of the venue where he was working. Instead of his usual night-time gig, this concert happened in late afternoon, while still light out. Did this change his style any? Nope. "Working clean" was not in White’s repertoire; between acts, he told the same ribald jokes he told to the grown folks at black clubs for years.

The crowd’s laughter could be heard clear to the lakefront. Even the children couldn't stop giggling; not because they understood the humor, but more because they weren't used to hearing cuss words uttered so casually, out in the open. Hi-Fi was a hit with the public, but White was never asked to play the festival again.

Born in Chicago in 1923, White came from an era when performers didn't specialize; the ability to sing, act, dance, and tell jokes were all required skills. White managed to make it to Hollywood a few times; Redd Foxx looked out for his old friends from the vaudeville circuit and had White guest star on Sanford & Son (1975), as well as on two episodes of the spinoff series, Sanford (1980-81). White’s resume also included appearances in two Penitentiary movies (1979 and 1982) as well as The Gong Show, where he appeared as a contestant, singing "It's All Right," the Impressions hit. White, like several comedians from his era (like Foxx), was a credible blues singer, and waxed the occasional single over the years, including 1971's "Bulldog" (on the Sandman label).

However, if a Chicago blues show, beauty pageant or drag ball needed some kind of host, White was typically the one selected to liven up the proceedings. His flamboyant attire ranged from long dresses to hot pants. With his 200-pound linebacker build, this wasn't something easily forgotten.

Despite his somewhat outré, feminine fashion sense, by all accounts, White was somebody you did not want to mess with. He was also expert with his fists, and if it came to that, a switchblade, as well. This author recalls seeing him preside over a multi-act blues show presented by local DJ Pervis Spann "the Blues Man.” This was at the UIC Pavilion in Chicago, in the spring of 1988. While several of his jokes were old enough to have whiskers, his timing ensured that we all laughed regardless.

Between bits, he'd point at random men in the audience who he claimed to have slept with. When he spotted three white guys in the all-black crowd, he asked the stage crew to shine a spotlight on them so we all could see; sure enough, they milked their moment, waving like they were on television.

Even though White is still remembered fondly around Chicago, his life wasn't documented as fully as Marchan's or Shane's. He was, however, one of the last of a showbiz lineage that also included Redd Foxx, Moms Mabley, Pigmeat Markham, Slappy White and other comedians who worked the chitlin' circuit on the edge of the R&B world.

From the 1970s onward, the dance music world extended and expanded the crossdressing scene, with artists like Sylvester, RuPaul, Katey Red, Big Freedia, and an entire subgenre out of New Orleans known as "sissy bounce." Long before it was common to be out and proud, Bobby Marchan, Jackie Shane and Wilbur White exposed their masculine femininity for all to see.

James Porter is a Chicago-based writer, DJ and musician. His work has been featured in such diverse magazines as the Chicago Reader, Time Out Chicago, Down Beat, and Roctober. He currently he hosts Hoodoo Party, a monthly radio program on WLUW-FM (wluw.org) focusing on early rock & roll, plus newer acts in the tradition. He is also the author of Wild In The Streets: Tales From Rock & Roll's Negro Leagues, a book about African-American rock musicians due next year from Northwestern University Press.